tetra-n-butylammonium tribromide in methanol; dichloromethane T=20°C;

in methanol

hydrogen bromide; dihydrogen peroxide in water T=20°C; 24 h; Irradiation;

lithium carbonate; lithium bromide in N,N-dimethyl-formamide

in diethyl ether; toluene 2 h; Heating;

1: methyl malonic acid diethylester With sodium hydride in N,N-dimethyl-formamide T=0 - 5°C; Inert atmosphere; 2: 2-bromo-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one in N,N-dimethyl-formamide T=-3°C; Inert atmosphere; 3: With hydrogenchloride in water; N,N-dimethyl-formamide pH=4 - 5; Inert atmosphere;

1: 2-bromo-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one With lithium hexamethyldisilazane in tetrahydrofuran T=-78°C; 0.25 h; 2: acetic anhydride T=-78 - 0°C; 0.5 h;

1: 50 percent / dimethylformamide / 20 °C 2: 83 percent / NaBH4 / methanol / 1 h / 20 °C 3: 54 percent / acetic acid; sulfuric acid / 4 h / 100 °C View Scheme

1: 2-bromo-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one 2: With toluene-4-sulfonic acid in benzene 3 h; Heating;